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The SHi Reaction at Silicon—A New Entry into Cyclic Alkoxysilanes by Armido Studer; Hanno Steen is a Chemistry article available to read on EtoBox.

What is The SHi Reaction at Silicon—A New Entry into Cyclic Alkoxysilanes about?

A new mild radical method for the preparation of cyclic five-membered alkoxysilanes is reported. This method comprises an intramolecular homolytic substitution reaction at silicon (S H i). Various leaving groups (SiMe 3 , GeMe 3 , SnMe 3 ) were tested in the homolytic substitution reaction. We found that high yields were only obtained for silanes bearing a trimethylstannyl functionality as leaving group in the S H i reaction. Rate constants for the cyclization reaction were estimated by conducting standard competition experiments. Based on the kinetic data, more elaborate reaction sequences such as radical addition reactions with a subsequent S H i step were carried out. Stereoselective cyclization reactions were also investigated. Excellent 1,2 diastereoselectivities were observed. The products of the S H i reaction, cyclic alkoxysilanes, can easily be converted to the corresponding diol derivatives by Tamao ± Fleming oxidation as demonstrated for several examples.

Who reads The SHi Reaction at Silicon—A New Entry into Cyclic Alkoxysilanes?

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Author
Armido Studer; Hanno Steen
Publisher
John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley (ISSN 0947-6539)
Published
1999
Language
EN
Field
Chemistry (Physical Sciences)

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